Winter dressing about finding that sweet spot between comfort, warmth, and a little bit of laid-back style. Our latest Timberland clothing collection makes it simple to pull together layered outfits that look good without trying too hard. From rugged men’s jackets built to handle the chilliest evenings to soft women’s sweats perfect for lazy weekends, every piece is made for real life. Whether you’re bundling up in cosy men’s jumper or throwing on a classic outer layer, Timberland has you sorted. This guide will help you mix, match, and make winter feel like the most stylish season of all.

Build your base with a logo crew

Start with an Embroidered Logo Crew, a soft, go-anywhere piece that feels as good as it looks. Pair it with relaxed dark jeans or tapered chinos and lace up some Allston Lace-Up Sneakers for a vibe that’s part sporty, part classic. Perfect for days when you just want to keep it simple and comfortable with a mood that says “maybe I’ll go out, or maybe I won’t”.

Layer up with some fleece

On those really crisp mornings, throw on the Newton Reversible Vest over your favourite long-sleeve shirt or t-shirt. The plush fleece brings all the cosy feels while the reversible design keeps things interesting. Pair with straight-leg cargo pants or chinos and step into the Lincoln Peak Lite Low Waterproof Hiking Boot for a fit that’s great for grabbing coffee or taking the long way home through the park.

Get streamlined and stay dry with the Caps Ridge Jacket

If you’re all about the clean lines, the Women’s Caps Ridge Waterproof Jacket is the move. Its 3-layered lightweight warmth and sharp cut layer effortlessly over crews and hoodies. Wear it with slim jeans and finish with the Women’s White Ledge Mid Waterproof Boot for a touch of rugged attitude that’s ready for puddles and downpours while still keeping you stylish.

Top off your winter look with accessories

The Tonal Embroidery Beanie is your go-to for keeping warm and tying everything together. If you prefer a cap, we have insulated, water-repellent caps with elastic cord make for easy, snug adjustments. Match them with dark denim or cargo pants and a pair of our iconic 6-Inch Timberland Waterproof Boots. Add a simple watch or crossbody Timberland bag to keep things laid-back, warm and polished.

Timberland’s men’s and women’s clothing collection is all about staying warm while looking cool. With the right jackets, a couple of cosy layers, and some classic Timberland footwear, you’ll be set for city strolls, country getaways, and all of the wintery fun in between.

Check out our range of winter ready styles online or head into your nearest Timberland store and try on our women’s pants and men’s sneakers with help from our friendly team.